Island Dreamer Sailing School Blog

Sailing on Island Dreamer is a blast, but it never hurts to be prepared.  Below are 10 things you’ll need to bring with you on your sailing adventure.

1. A Good Book.  Ideally, a book that has nothing to do with your real life.  Seduction of the Minotaur or Like Water for Chocolate are two excellent choices, or, on the other end of the spectrum, anything by Carl Hiaasen.
2. Sunscreen.  Normally, I’m anti-sunscreen, but no one is getting any younger and with the reflection from the water, the sun is stronger than your realize.
3. Moisturizer. See above.  Stock up on After Sun Lotion and Baby Oil.
4. Music. This is key.  You will need a good soundtrack for your vacation.  Take the time to create a “Vacation Playlist”.  Think soulful, rhythmic, and jazzy.
5. Bathing Suits. As a general rule, you’ll want at least one per day.
6. Sarong or Sundress. Make your life easy and buy something simple, colorful, and comfortable.
7. A Cute Hat or Scarf. Unless you like the frizzy wind-blown look, you’ll need something to tame your tresses.
8. Wine. Who are we kidding?  Wine is good! A couple of bottles of your favourite Chardonnay or Pinot will be sufficient.
9. Sunglasses. Don’t bring your best pair, and be sure to bring  back-up.
10. Conditioner. The sun and saltwater will dry out your hair. Leave-in conditioner can be a life saver.

NOTE:  One thing NOT TO BRING is jewelry.  You do not want your emerald cut solitaire going overboard.  Leave your irreplaceable jewels at home.

Nestled in an out-of-the way area in the heart of Marathon is a small marina and mooring village along Boot Key Harbor. It is the home of Sombrero Marina and the world famous Docksides Bar.

The locals gather around the grand wooden bar at all hours, from breakfast until last call, listening to the radio and watching the weather reports on TV. The marina is always buzzing with activity. And when the sun finally sets, you can hear the call of Conch shells celebrating the end of the day and the promise of the night to come.

But late at night, strange things have been know to happen in the harbor, I’ve actually seen a man tow a dinghy — swimming across the harbor holding the rope between his teeth because the motor had broken down.

Late at night, it’s eerily quiet crossing the harbor over to the sail boat. It’s easy to get lost in your thoughts. The sky and water are the same shiny black ink. It’s at those moments that I often wonder where the name ‘Boot Key Harbor’ came from.

According to legend, a stylish young woman, visiting from up north, her feet tired from dancing all night at the Brass Monkey, took off her very expensive boots with 4-inch heels and tossed them one by one into the harbor during a 3am crossing. According to the story, somewhere, at the bottom of the harbor is a size 6 pair of Valentino black suede stiletto ankle boots mysteriously still in pristine condition.

Every once in a while, I think about those Valentino boots and what they must have meant to her and how she could have let them go so easily.

…at least for a week, see how it goes.  Hop a flight to Miami, board Island Dreamer, and head to the Keys.

The first thing you’ll notice is how the sound of water gently lapping against the side of a sailboat will put you to sleep.  Even as the sun is glistening in shards of light off the ocean, as far as you can see, it only acts as more incentive for you to close your eyes.  Sounds become muted and the moments before you arrived are now a faint memory.

What you are feeling now is “Keysey”.  The stress you used to feel, that panic in the pit of your stomach has dissipated and evaporated into a miasma of sunlight and ocean breeze

What’s that you hear?  Steel drums or is it Steely Dan? How long has that rum drink been in your hand? (and, does anybody really care?).  The warm air tickles your bare feet as you reach for that Travis McGee novel (no judgment here, it’s cool).

Dolphins are free associating with the water over to the port-side; seagulls are flying close by, laughing at them.  You could get used to this.

By the time this week is up, you are a not the same person who boarded the boat.  Your batteries have been recharged and nothing is a big deal.

Decision time:  Can you adopt a stress-free lifestyle?

I want to welcome my sister Jodi as a contributer to our blog.  I have been very busy this season doing couples sailing classes, I have not not had much time to post.  Jodi has agreed to give some of her perspectives about sailing and the Florida Keys.  Enjoy!

I picked up the August, 1957 Popular Boating Magazine at an Antique fair on South Beach.  From an ad by the National Sailing Association;

Skippering a sailboat builds character. It teaches responsibility, dexterity, ingenuity and good sportsmanship. It attracts companions with equally high ideals. Young sailors are rarely troublemakers.

What an argument to teach your kids sailing! Imagine what they would have had to say about video games and computers.

There is lot’s more cool stuff from the magazine I will post soon.

Young Sailing Skipper at the Helm

I was interviewed for a business magazine about turning your hobby or passion into a business.  One of the questions asked was what mistakes have you made. I had a hard time answering last night, this morning as the sun was coming up I sent her this follow-up;

When I was in my early 30′s  I considered getting my captains licence and pursuing a career on the water. Deep down I knew that this was what I wanted to do but the security of a land based business career made me afraid to follow my dream. So maybe my biggest regret is that I didn’t try to follow my dreams earlier.

As the saying goes, today is the first day of the rest of your life.  There is no better time than now to try something new.

Boca Chita Harbor at sunrise

We have had 3 customers (so far) that have taken the time to post reviews on yelp.com. In case you missed them;

Wes N writes;

We just returned from our four day couples sailing course and it was a wonderful (and unique) experience. Our goal was to achieve the ASA 101 and 103 certifications, and with Harold and Margie’s help we did it with time to spare. Both of the Ochsteins are skilled sailors, patient teachers, and have an encyclopedic knowledge of the local waters in the Keys and the Miami area. We got plenty of sailing time in the big 41′ Island Dreamer  and also in their smaller (and less intimidating) 21′ boat, and still had time for a couple of fun evenings on shore. A bonus was the chance to see some of the local flora and fauna up close and personal – a big sea turtle, half a dozen porpoises, and and endless variety of birds native to the Keys. The calm, broad, shallow waters of the Keys turned out to be ideal for a couple of newbies with no sailing experience. What really makes this different from the average sailing school is that Harold and Margie aren’t just good instructors; the Island Dreamer is also their year-round home (they live aboard), and we got to know these lovely and hospitable people very well by the end of our trip. If your taste in vacations runs to the intimate bed & breakfast experience, and you want to become a confident sailor, you’ll love the Island Dreamer experience. If you’re more the Marriott type, or think that twelve meals a day on a huge cruise ship is the perfect holiday, then you may want to think again; Island Dreamer (and sailing in general) may not be for you. It was perfect for us.

David B;

The Very Best!!!!!!!!  Harold and Marge are the friends you have always known but you just haven’t met yet.  The sailing and navigation training is the best you can recieve.  The experiance, well I was lucky enough to learn more about myself.  If you don’t go sail with them you are missing one of life’s special moments.  David & Deanne Benn 2010

Peter C;

WOW!!!!!!!  What an awesome experience.  Capt’s Harold and Margie taught us so much of what we needed to sail safely, while offerring up great food and a terrific time.  Would do it again in a heartbeat!

Highly recommend their service. Go for it………

Thanks so much!

Margie and I sold our house in 2001 and moved aboard our sailboat. Even though we had owned boats for the 25 years prior to that and spent most of our leisure time sailing and diving it still was a big step to leave a land based life. I spent an quite a bit of time reading up on the cruising life before we left, getting different perspectives of the possibilities of the liveaboard lifestyle helped us to shape our goals.  I just ran across an informative website about making a sailboat your liveaboard home, Mark  has some great thoughts about becoming a full time cruiser.

One of the great things about sailboat cruising is the freedom to choose not only your destination but also how you get there. The more you know about life on board before you leave the easier it will be for you and your partner to really enjoy cruising long term.  Happy reading!

Cruisers in Israel

When Margie and I leave Miami to sail to the Bahamas one of the scariest parts of the trip are the lights of a big ship heading towards us. The recent development of AIS has made this passage much easier. AIS transmitters are required on all boats over 150′ and optional on smaller boats. They give the location, heading and the name of the boat and are broadcast on a VHF radio frequency with a range of 20 to 30 miles. If you have a AIS receiver on board it can interface with your chart plotter or be a stand alone unit.  Now you can you see where the ships are going in relation to you and if you have a transmitter they will see you. It is also easy to contact them on the radio because you know their name.

You can a live feed from our area below;

Margie and I will be helping Captain Jean and Captain Jeff with the Couples Cruising Seminar in Annapolis October 9. It will be a great way to learn more about cruising from a group of very experienced sailors;

The goal of the Couples Cruising Seminar is to give you the tools and perspectives you need as a couple to safely pursue the cruising lifestyle. We have assembled an outstanding group of marine professionals who have varied experience and back ground to present you with a balanced educational experience

Here is the Schedule;

8:00   Sign in and Continental Breakfast
9:00   Together planning your dream – Create your own guide to the cruising life.
10:00    Boat & equipment choices – What makes a boat easy for just two?
11:00    Developing the partnership beyond pink and blue – Teamwork,
dividing the management of the boat and seamanship skills.
12:00    Break for Lunch
1:30   “The Fear Factor” let’s talk about our fears. – Emergencies at sea,
sailing at night, open water passages and bad weather.
3:00   Voyage planning & Weather routing – Know when to go
or maybe change the route for smooth sailing.
4:30   The Cruising Lifestyle – A look at successful couples cruising.
Comfortable Cruising.
5:30   Q&A, Discussion and Social Hour